Digitization is becoming part of agriculture. Winemakers can use monitoring technologies to map land or control the quality of grapes, and telematics, e.g., in tractors, or use entire autonomous machines. The aim of this paper is to find out the barriers to and benefits of the use of smart farming technologies by small and medium winemakers, specifically sensors and weather stations, which allow the collection of site-specific data for subsequent application in viticulture. Therefore, the pilot study analyses how winemakers in traditional industry are able to employ smart farming technologies (SFT) to gain some benefits and also describe possible barriers. The primary method of data collection was through 27 semi-structured interviews with relevant wine industry actors, accessing documents created by SFT providers and an academic literature review. Three groups of actors were researched: 1) 22 winemakers including the Ekovin Association, 2) three SFT providers and, 3) one supplier of hardware for soil and temperature sensors. According to the information of winemakers, it is clear that SFT are used by some of them and they are clearly aware of their benefits, which is also confirmed by SFT providers. The findings revealed that the main STF benefits are adjustment of the product portfolio, savings, consulting and organization of activities. However, respondents also mentioned barriers to SFT implementation, such as low need for information, another source of information, conservative approaches, ignorance of SFT, financial demands, low state support and age of winemakers. The novelty of this paper is in providing an analysis of the issue of SFT, specifically sensors and weather stations, for winemakers from three different perspectives, that of winemakers, suppliers of SFT and HW manufacturer for SFT.